Unexpected decomposition in the reaction of bis(2,4-dinitrophenyl) oxalate with water

Add time:08/10/2019    Source:sciencedirect.com

The kinetics of the hydrolysis of BIS(2,4-DINITROPHENYL) OXALATE (cas 16536-30-4) (DNPO) were studied by infrared spectroscopy. The changes in the carbonyl region showed that neither 2,4-dinitrophenyl hydrogen oxalate nor oxalic acid could be detected. Simultaneously, the rate of evolution of carbon dioxide was measured in the reaction mixture and found to be equal to the disappearance of DNPO. Analysis of gaseous products confirmed the liberation of carbon dioxide and carbon monoxide but their ratio did not match that from known reaction pathways. With diphenyl oxalate and phenyl 2,4,6-trichlorophenyl oxalate, hydrolysis to phenyl hydrogen oxalate was detected. On the basis of these observations a new reaction scheme is suggested that describes both hydrolysis and decomposition of the oxalates.

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